


How to NOT Set Someone Up: A Story By Gabriel, Jimmy, and Sam

by TimeToTravel



Category: Supernatural
Genre: Alternate Universe - College/University, Alternate Universe - Modern Setting, Castiel and Jimmy Novak are Twins (Supernatural), Crack, Cute, Established Castiel/Dean Winchester, Fluff and Crack, Gen, Happy Ending, Hijinks & Shenanigans, M/M, Protective Gabriel, This Is Why We Can't Have Nice Things, Why Did I Write This?
Language: English
Status: Completed
Published: 2020-02-26
Updated: 2020-02-26
Packaged: 2021-02-27 19:08:09
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 6
Words: 6,044
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22900708
Author URL: https://archiveofourown.org/users/TimeToTravel/pseuds/TimeToTravel
Summary: When Jimmy notices Castiel acting oddly at Ellen's Coffeehouse, he decided to do some investigation. Along with Sam and Gabe, the three meddlesome brothers discover the joys of Destiel. Inspiration from TheBadassIsIn's fic, The Whole Damn RoadHouse Knows. It is amazing, so check it out.Excerpt:“I’m sorry to break you out of your coffee fantasies, but my first class has almost started.” Castiel gets up from his seat across from Jimmy moving towards the door, coffee of bliss in hand, seeming unusually excited to get to first period. Well, that wasn’t suspicious or anything. As his brother’s figure disappeared among the crowds of bustling students, this meddling kid vowed to get to the bottom of this mystery. Squinting his eyes in suspicion, he took another sip of his coffee, face immediately lightening up at the blissful taste of the beautiful work of art. Forgetting about his investigation, he continued drinking in the peaceful buzz of the cafe.”
Relationships: Castiel/Dean Winchester
Comments: 2
Kudos: 37





	1. Jimmy Swears On His Coffee

**Summary for the Chapter:**

> Jimmy had frequented Ellen's Coffeehouse on multiple occasions, but this was the first time he took his anti social twin with him. Suspicions arise as Castiel seemed to be happier, and Jimmy was going to get to the bottom of the mystery.

When Jimmy Novak dragged his anti-social, people hating, reserved twin to the local coffee shop on the campus of KU, he had expected a lot of things. They were, in no particular order, a grumpy grinch, incessant begging to go home, a complaint here and there about what they were doing at a coffee shop when the brewer in their apartment was ‘quite adequate’, i.e. that it was spewing tasteless brown liquid that one might assume to be coffee under the right circumstance (whilst drunk, stoned, or sleep deprived), the face Castiel makes with his brows pinched and eyebrows narrow, glaring at the people he hates, or a weird combination of the four. 

Granted, he did get the weird combo on the way to the coffee shop, but was utterly shocked with the shift in his mood sometime after he had begrudgingly ordered their drinks stating that it was to, “prove that he was the better twin.” That was a statement that he had to disagree with, as he was the one who had to continuously look for ‘random’ occurrences of social interaction for Castiel to ‘stumble upon’. The two were quite different in those ways, Jimmy being a ‘little more’ of a people person than Castiel, who thought that the entirety of the human race was an abomination, although they both shared the unfortunate habit of using far too many air quotes to be ‘normal’. 

Anyway, back to how weirdly uncomplaining Castiel seemed to be, sipping on a French Roast Coffee that was, “as dark as the void where his soul meant to be before noon,” at Ellen’s Coffeehouse, or the best coffeehouse KU ever had the pleasure of tasting. Jimmy had frequented the place quite a bit during the last year of his undergrad, coffee making up 60% of his body’s water content as final’s week had approached. It was two years since Ellen and her coffee had saved his ass, Jimmy wipes an imaginary tear from his eye as he recollects the haggard state he’d been in that fateful day. 

“Are you feeling okay today?” Castiel tilts his head in inquisition. 

Jimmy, shaking himself out of his coffee fantasies responds. “Shouldn’t I be asking you that, Mr Sunshine and Rainbows? Did they spike your drink or something, cause if it makes you this happy it must be one hell of a trip.” 

Castiel looked down for a moment and-was that a blush?! Jimmy couldn’t help a bubble of excitement from pulling a smile onto his face. One of the baristas had thawed his brother’s cold exterior. Who knew that one coffee shop visit would change Castiel in such a way? Well, Jimmy did. Ellen’s Coffeehouse continued to work it’s miracles, he guessed, saving his sanity and his brother’s social life, both incredibly difficult tasks to manage.

“Ooh, Cassie made a friend,” Jimmy said, hiding his face behind his Full City Roast that was, “a perfect balance between bitter,” he pointed towards Castiel, “and so much sugar it will rot your teeth and call itself faerie dust,” he directed towards Gabriel, who had, at that point in time, consumed so much sugar that if he were a regular human being, he’d have been passed out on the couch, groaning as the sweet addictive powder gnawed at his insides, and god he was getting off track. 

Castiel turned back into a grinch. “How many times must I say that ‘Cassie’ is a nickname that I do not find enjoyable.”

“Ah, but if brother’s only did things the other enjoyed, then it would be like being strangers, and who wants that?” Jimmy pointed, leaning back in his seat. “A brotherly bond is special, and filled with annoyance and irritation. Bothersome nicknames are an important facet of that bond.”

“You use words such as facet, yet the thought that you could stop calling me ‘Cassie’ is unfathomable.”

“The two have nothing to do with each other.”

“You, have nothing to to with each other.’” The poor attempt at a comeback forced Jimmy to hide a smile. 

“That didn’t even make sense,” he said before tilting his head back in laughter. Catiel joined him as well in the hysterics. 

As the laughter died down, Jimmy took another sip of his drink, tilting his head back to let out a groan. “Ellen, you’ve done it again,” he gazes at the coffee in admiration. “If I believe in anything in this world is this coffee.”

Castiel took this as an opportunity to intercede. “Tell that to the shrine in your room. If you haven’t already, you’d probably sell your soul to be one with the coffee.” He imitated Jimmy, quite poorly might he add, raising his voice an octave. “‘Oh, coffee! Holy Coffee! I want to be one with thee, burn me and mix my ashes into the beans so I can finally be one with my true love.’” With that, he planted a dramatic shooch on the paper cup, caressing it to his cheek. 

“Fair enough, but i wouldn’t want to be mixed with the beans. If anything, I’d totally be mixed into the final brew. I can see it now.” Jimmy trailed off, looking towards the ceiling. Oh, what a wonderful life it would be as a coffee at Ellen’s Coffeehouse, delicious, creamy, delightful-

“I’m sorry to break you out of your coffee fantasies, but my first class has almost started.” Castiel gets up from his seat across from Jimmy moving towards the door, coffee of bliss in hand, seeming unusually excited to get to first period. Well, that wasn’t suspicious or anything. As his brother’s figure disappeared among the crowds of bustling students, this meddling kid vowed to get to the bottom of this mystery. Squinting his eyes in suspicion, he took another sip of his coffee, face immediately lightening up at the blissful taste of the beautiful work of art. Forgetting about his investigation, he continued drinking in the peaceful buzz of the cafe. 

It would be a month since the first time Jimmy had towed Castiel to Ellen’s Coffeehouse and noticed how much happier Castiel seemed to be. A month of daily bliss shared with his anti social, becoming more social brother. The ‘suspicious behaviour’ continued throughout the days, Castiel being more open to interaction, complaining less, but still insisting that he was still, ‘as people hating as ever.’ 

Jimmy thought otherwise. 

Cassie may have been growing out of his shell, but he was still going to find who had done this. Throughout their childhood, Castiel had never ‘liked’ anyone, preferring studies and sarcasm to human communication. The only people he had ever really talked to were Jimmy, Gabriel, and Meg, his grumpy black Bombay with floppy ears and a resting bitch face. Castiel said it was, “quite endearing,” while every other sane person would have said that she was a demon spawn. She sure was chaotic enough if the scratches lining Jimmy’s body said anything. But Castiel loved the ball of fluff, insisting that she was, “just misunderstood,” and was, “really cute once you get to know her.” 

Cat tangent aside, Jimmy was going to find the source of Castiel’s happiness if it was the last thing he would do. And, you know, do the usual ‘make sure they are good enough for him’ check. Maybe pull a quick ‘vibe check’ for maximum sibling douchiness. 

Sipping at the delicious caffeine-ness of the coffee and munching on piece jalapeno cheddar bread, he stared off into the distance, imagining the ways he could ensure this person was good for his favorite twin. 

“I’m your only twin?” 

Jimmy looks up in confusion before his eyes light up with comprehension. “Oh! How much of that did I say out loud?”

“Something about a person being good enough,” he bit into chocolate cherry bread, claiming that it was to, “offset his bitter self.” Placing it back onto the plate, he spoke. “Whatever you’re thinking of doing, please don’t do it.”

Now, at this point Jimmy was not listening to Castiel and had instead continued to plan how to do just that. Something along the lines of stalkage, he thought, but before he could quell his curiosity any farther, he should probably let Gabriel in on it. After all, he is basically a prankster god.

**Notes for the Chapter:**

> Thank you for reading:) And thank you for everyone who read my first fic, Two Estranged Angels and The Winchesters! I really appreciate you guys:)


	2. Gabriel Notices Something

**Summary for the Chapter:**

> Gabriel begins to notice Cas’ odd behavior as well.

Gabriel had lived a long, full life at the bakery, having opted out of his plan to get a doctorate in exchange for A Slice of Heaven. For the longest time, he had been working towards his doctorate in Anthropology before saying, “Screw it, I wanna be a baker,” and then consequently dropped out and opened his bakery. On the bright side, the place was mouth wateringly delicious with beautiful pies such as An Apple A Day, You’re The Key To My Lime, Blue Da Ba-rries, and the ever famous Not Today, Satan, a gorgeous cherry pie with a pentagram crust inlaid with enochian script courtesy of the Forgein Language class he had to take. 

Anyway, beautiful pies aside, throughout the entirety of his life, he had never seen his brother so happy. Castiel to be specific. The biggest shock seemed to be that the person who was responsible for was, well, a person. Cassie, i.e. the literal definition of a social recluse. No joke, Gabriel was certain that he had only one friend not including his brothers, so obviously, he was interested when Castiel was practically bouncing on his way to the bakery on a Thursday unlike no other. 

“What’s crackalackin, Cassie?” Gabiel leans over the counter. “They spike your drink at the place Jimbo took you to?”

At that, Castiel tilted his head. “Why must all of you assume that there was some form of drugs present in my coffee?”

With a nonchalant shrug, he responded with. “I don’t know, maybe because the only time you look like there is any life within you is when you’re with that demon cat.”

Castiel looked offended at the comment, placing a hand dramatically on his chest. “How dare you insult Meg! My baby! The light of my life! The only thing that brings me joy!”

Well, it looked like Castiel had a new ‘light of his life’, or at least that’s what Gabriel had thought. With the sunshine exuding from every orifice of his body, Gabriel was certain that someone was involved and he was getting to the bottom of this. “Anyway, who injected you with liquid sparkles?”

Castiel cleared his throat. “No one injected me with ‘liquid sparkles’,” he added air quotes around the phrase, like always. “At least you didn’t jump to conclusions like Jimmy.” Right after those words escaped his mouth, he regretted it. Curse having a brother who collects blackmail for fun. Letting out a quick sigh, he turned back towards his brother, who’s smile had just grown three sizes. 

“Don’t conclude that my assumptions are any better than Jim-Jam. I still think you found your one, true love,” Gabriel twirls a rolling pin in his hand. When he figures out who this mystery person is, Gabriel would totally embarrass him. Alas, that was what brothers were for. 

“Whatever,” Castiel gives up, grabbing a slice of pie before stuffing it in his mouth. “Delicious as ever Gabe.”

“You bet your ass it is.” The bell to the store chimes as Cassie strolled out to his afternoon classes.

A month after Gabriel’s suspicions began, Jimmy stormed the bakery claiming, “Something’s up with Castiel!” His regular college clothes were a sharp contrast to Castiel’s usual trench coat and suit get up. Man, the kid was obsessed with the trench coat, but in any case, Jimmy was storming the bakery. 

“There’s a lot of things Castiel’s up to, but I’ve got a feeling we’re talking about the same thing.” Gabriel rested a hand on the counter, leaning forward like a teenage girl. “Now, spill.” He batted his eyelashes at Jimmy. 

Jimmy mirrored his moves, leaning onto the counter. “So, Cassie definitely is meeting someone.”

“I know right! Totes a ‘good friend’.”

“I can hear the air quotes in that statement. God, what is with this family and air quotes?” Jimmy throws his hands up in question.

“I have no idea. Anyway, what else?” He continues batting his lashes, Jimmy joining him again at the counter. 

“So, today he shows up Ellen’s Coffeehouse again today, right?”

“Uh huh.”

“And he actually interacted with a human being.”

Gabriel raises a hand to his chest doing a great impression of grandma clutching her pearls. “No way.” And it was true. As long as the brothers had known Castiel, he was an awkward, anti social, people hating burrito who’s only love was that grouchy old cat, Meg. Not even Gabriel could have brought him out of his shell, and Gabe brought Michael out of his shell. Granted it was because he just so happened to meet Adam, but, hey, Gabriel still takes credit for it. 

“Yes way,” Jimmy spooned a piece of pie into his mouth. “I bet he’s in Cassie’s first class too. You should see his face when he heads there every morning. And at Ellen’s Coffeehouse. I bet they’re a barista there.” 

“Stalk ‘em?” Gabriel asked, hanging this apron on the hook behind the counter. 

“Stalk ‘em.” 

And with that, the two brothers hatched a plan. The next day, they would shadow Castiel to get to the bottom of this mystery, scooby doo style. The stuff they came up with was comedy gold too.

**Notes for the Chapter:**

> Thank you, my dudes! :)


	3. Sam Knows, I Guess (He Had To Ask Jo)

**Summary for the Chapter:**

> Sam had been noticing Dean’s strange behavior and had given into to asking Jo what was up.

Sam Winchester

Unlike the Novaks, Sam was a lot slower to notice the signs, though slowly, he began picking up on the cues. Dean, for one, had definitely begun to look a lot happier in the past month, especially after his morning shift and classes. Now, Sam wasn’t one to jump to conclusions, but he was certain there was something going on. One fateful Tuesday, he finally gave in, pulling Jo aside during their afternoon shift. 

Placing his towel on the bar behind the counter, he started to talk. “Have you noticed Dean acting a bit weird lately?”

“If I did would you continue doing your job?” she shot back to the moose, not looking up from the register. 

“No, I’m asking honestly. Don’t you notice anything weird during the morning shift?” 

Jo stared him dead in the eyes, threatening enough to make even the 6’ 4” giant quiver in fear since childhood. Joana Beth Harvelle, little sister to Sam and Dean since childhood and master of Death Glare™. When one has faced the Death Glare™, one has survived all. At least that’s what Sam believed to be true, or anyone else who had the pleasure of meeting angry Jo. The glare slowly turned into contemplation before nodding in agreement. “There was this customer. He comes every morning with his brother.”

“A customer, huh?” Sam leaned against the counter. “Tell me more.”

Jo turned to face him, the register forgotten. “So, really polite guy, kind of on the weird side shows up like a month ago. Dean’s whole face brightens up, starts talking to this guy, Cas, I think, about the Latin Class they have together first thing in the morning. Everyday they chat up a storm, it’s disgustingly adorable. Those two are the most tooth rotting fluffy things I have ever seen.”

“Woah,” Sam moved back, hit with a wave of shock. That would explain it. He was certain that Dean had found a friend and he was ready to get to the bottom of the mystery. Dean never had many friends when growing up, taking care of Sam instead of focusing on friends. Their father was quite neglectful, an chronic alcoholic ever since their mother had died in a house fire. Thankfully, after Dean got into college his friend group expanded to include Charlie, who Dean said was, “the little sister he never wanted” before looking towards Jo and saying, “I didn’t want you either, so don’t get any ideas,” and this Cas guy. 

Don’t get him wrong, Sam was ecstatic that Dean found a friend, but seeing is believing and Sam Winchester was going to get to make sure that Dean wasn’t going to get screwed over, and hey, if nothing was wrong, at least he’d get in some good old brotherly fun. 

Coincidentally, or due to the author wanting to write some shenanigans, the plan that the meddling siblings had come up with were quite similar. 

Sam, Gabe, and Jimmy’s Foolproof Stalking Plan

Step 1: Go to Ellen’s Coffeehouse in the morning and quietly observe

Step 2: Follow them to Latin I

Step 3: Ensure the friend wouldn’t break their brother’s heart 

Step 4: In case dude’s a dick, rip their spine out

Step 5: Get the hell out before they die

When Sam had arrived at the coffeehouse the next morning, he expected to get caught by Dean, not a conspicuously inconspicuous tiny man (at least from the perspective of the cossall being that is Sam Winchester. From normal human standards, the “tiny man” was actually an average sized person at 5’ 8”). The man in question adorned a beautiful glasses fake nose mustache combination, like one of the ones used in comedy shows as a poor disguise. The only difference was that this was real life. 

Fake glasses rapidly towards Sam then himself. “Psst, you.” Sam pointed to himself in question. “Yes, you, blatantly staring at the door.” Hesitantly, he stood from his position in a booth and scooted over to tiny guy. Leaning towards Sam, he asks. “Who are you stalking?”

“Who says I’m here to stalk anybody?” he shot back defensively. 

“I may look like one, but I’m not an idiot. You’re staring at the door just inconspicuously enough that you don’t want to be seen, so the only logical conclusion to draw would be that you are stalking someone,” he stated, not looking back at Sam as he continued searching for a person. 

Surrendering, Sam spoke. “Fine, you caught me. I’m waiting for my brother’s new friend to come in. Make sure he’s cool, you know?”

The guy moved to say something else before the walkie talkie-seriously?- crackled to life, a voice stating, Keep and eye out, we’re headed to the coffeehouse, and then more quietly, Ellen, please don’t take away my free coffee on Finals week away. They’re the only thing that keeps me alive. And with that, the message ended, leaving the two overprotective brothers in silence.  
Turning back to face Sam, glasses spoke once more. “You too? I’m here to meet my brother's new friend too. Small world.” He turns to face the door as two identical people walk into the coffeehouse. “There he is.” Glasses point to the trench coat wearing twin heading towards the counter as the other one moved towards the table in front of them. 

The other twin turned around, facing glasses and Sam and asked. “Plan go? You paying attention to Cassie?” He turns to face Sam. “And hello. Are you one of Gabriel’s friends or are you doing some stalking of your own?” Sam recognized his voice. It had been the same one on the radio. 

“Why does everyone assume I’m stalking someone?” Sam asked exasperated. The guy opened his mouth before Sam stopped him. “Nevermind. I am stalking my brother, and someone’s talking to him.”

Indeed, there was someone talking to him. It was none other than the trench coat wearing twin that glasses-Gabriel- was stalking. Well, that took a turn. Sam turned to face glasses, and other twin, shooting them an incredulous look. He pointed towards Dean, who was leaning over the counter chatting with trench coat. “That’s my brother, and I guess that’s your brother.”

And that’s when Gabriel began singing “It’s a Small World,” with backup vocals by the other guy, Jimmy, he learnt later. Due to the obviously cliche and humorous circumstances and due to the fact that the author can’t think of a better way to skip to the next situation with many more shenanigans, Sam burst into hysterics joining into the singing.

**Notes for the Chapter:**

> Thank y’all!


	4. Three Meddlesome Brothers Make Pranks

**Summary for the Chapter:**

> The three meddling brothers get a bit schemes. True to fashion, plans are made and pranks are discussed

Later the three meddling brothers had regrouped at Gabriel’s apartment as they had all, i.e. Jimmy and Sam, skipped out on classes in the assumption that they were going to stalk all day. Although the part about stalking was unnecessary at this point in time, the brothers still had to do some private investigation to make sure the other guy was, “right.” The guys had slowly buried themselves into the cramped apartment kitchen, and began to bake because why the hell not. 

“So, let’s get this straight,” Sam said, leaning against a banister (wow, he does that a lot). “They totally belong together, right? I mean, Dean hasn’t acted like that since,” he hesitates. “He’s never acted like that.”

The answer comes simultaneously as both Jimmy and Gabriel both say, “No shit, Sherlock.” 

Gabriel popped a Jolly Rancher into his mouth. “Sooo, we’re totally going to come up with a series of crazy shenanigans to get them together, right? Total rom com style and everything.” He kneaded the dough at hand, beginning to roll it into a thin sheet. Wrapping it into a sheet of plastic and setting it aside to set. “Any thoughts?” 

Sam snapped out of his daze, turning to face Gabe as Jimmy said, “Ellen’s coffee do they like each other. By the way, I’m totally vibe checking, your brother.” He looked at Sam at the last sentence, staring pointedly. 

Sam sent a quick, “I’m cool with that as long as I can get them drunk and lock them up together.” A smirk appears on his face. 

“Oh, you’re evil. A genius, but evil,” Gabriel shook his head, furiously adding a sugar and cornstarch mixture to a pot of heated cherries. Adding a hint of salt to, “keep the demons away,” and to lessen the overwhelming taste of sugar. (Don’t actually take my advice for this, the author is not a baker and cannot cook without burning down the kitchen. If anyone wants to put some pie recipes in the comments, the author will gladly fix it), Sam whipped his head to stare at the beginnings of cherry pie filling and smiled an scheme-esque smirk. Gabriel looked up in confusion before it turned into an equally meddling smile. “Question, does Dean like pie?”

Sam snorted at that comment. “Like pie? That may be the biggest understatement I’ve ever heard. Practically worships pie. If it were legal to marry pie in Kansas, I swear, he’d marry in a heartbeat.” 

“Castiel works night shifts at the bakery, so if you could bring Dean-o over I could set up a pie filled dream one can only imagine of.” Gabriel twirled the wooden spoon in his hand for dramatic effect. “One taste of my beautiful creations and that boy will be so far in the love train that there’s a high possibility of marriage at my bakery.”

“For whom, Cas or the pie?” Jimmy leaned over the counter. 

“Knowing Dean?” Sam chortled, smiling slightly at the thought of the scenario playing out. “Probably both.” Oh, Dean was gonna kill him when he found out, but it was worth it to see his brother happy. Turning back to the Novak’s he wrote down the steps for, “Operation Destiel.” 

And so, the boys created their plans to be executed periodically throughout the next week. Thursday, Jimmy would check Dean out and make him think about Castiel before, later that evening, he’d offer to visit A Slice of Heaven, a bakery owned by his older brother. There, Castiel and Dean will see each other and start talking when Sam would walk in and join the conversation, asking to go out for drinks Friday evening. Some “random accident” would then occur, leading to the two drunks stuck to talk out their feelings and boom. Operation Destiel would be declared a success. Sam could see the whole scenario playing out in his mind. Quelling his excitement, he worked with Jimmy and Gabe to work out the kinks. (This is 666)

**Notes for the Chapter:**

> Thank you so much for reading this chapter:) This chapter is relatively on the short side, but it’s some schemes boys and the word count is 666, so I think it’s okay P.S. If anyone has any legitimate cherry pie recipes, comment them and I’ll edit it:)


	5. Operation Destiel: Smooth Sailing...Mostly

**Summary for the Chapter:**

> Jimmy, Sam, and Gabe’s plan is set into motion, vibe checking and all.

Dean Winchester 

The day had begun as normal as usual. Awake and ready, though not willingly, by 5am at Ellen’s Coffeehouse like always. Dean rested his elbows on the counter, watching groups of people rushing in to get their morning coffee before school. Multiple people were frantically clacking at their keyboards in a hasty attempt to finish their papers before the due date at 6:59. He quite liked his job at Ellen’s. She was practically his adoptive mom at this point. Wow, Bobby and Ellen had to get married. 

Shifting focus onto something other than the closest things to parents he had love lives, he began preparing another drink for what looked like a student who had a test today and had studied for the past week and a half without leaving their dorm/apartment to ensure that they would pass otherwise known as a sleep deprived caveman in sweatpants. He was pretty sure the number of shots of espresso was going to kill someone, but, hey, he didn’t get paid to be questioning other people’s life choices, so 14 shots it was. 

“Here’s your order,” he handed the guy his coffee, who, might Dean add, looked as though he’d just handed him his will to live. “Thank for shopping with us-” 

“VIBE CHECK!” a voice rang through the coffeehouse, leaving many caffeine induced students jumping from their seats. The door banged open against the wall, clearly directed towards Dean as the person, blurred by the the darkness outside, was pointing towards him. 

Shit, what’d I do this time? He turned to face the figure. The blur reduced to reveal-

“CAS?!” 

What the fuck? Why would Cas do this? Cas would never. Dean’s mind raced before he noticed Cas’ clone-wait, it had to be Cas’ caffeine loving, Ellen worshipping, non trench coat wearing twin, Jimmy, he thought his name was. And he was talking to him. Shit, great first impression, Dean. 

“-so sorry to disappoint, but I’m Jimmy,” he continued. 

“Cas’ twin, right?” Dean asked, trying to remember what Jimmy usually ordered. Full City Roast! He began prepping the drink for Jimmy as he paid Jo at the register. He moved to talk to Dean. 

“Yesh, that’s me,” he said as Dean handed him his drink. “And your Cassie’s friend, right? He talks about you often. Been a lot happier since he met you too.” 

Dean couldn’t help the rising fluster before squishing it with whatever willpower he had left. “He talks about me?” 

“Yeah.” he sips the drink. “Amazing drink by the way. So, how did you two meet anyway?”

A smile appears on Dean’s face as he remembers the memories. “We met at Latin I and both expressed an interest in the subject along with some classic novels. It was great, you know, having someone to talk to about anything,” he turns to look around for a moment. “Where is Cas anyway?” 

“He was busy studying for an exam this morning.” Surprisingly, Jimmy was telling the truth. Castiel truly was studying for an exam in the afternoon and the timeline had somehow managed to work out well (or the author wants the pie heaven to begin, you choose). He looked down at his watch, and true to timing, Jimmy’s Psychology Club meeting was going to begin in a minute. “Hold on, I’ve got to be at school now. Can we continue this conversation over pie at A Slice of Heaven? My brother owns the place, so unlimited pie” 

True to Sam’s word, Dean’s eyes lighted up the mention of pie. “I could never say no to free pie.”

As Dean arrived in Latin, he sat by Cas, like always. The two began working in a comfortable silence built up through a semester of friendship. Jerking his head up sharply, Dean glanced at Cas with a quick, “Oh.” Castiel turned, focusing his beautiful midnight ocean eyes on Dean. “You’re twin, Jimmy talked to me at the coffeehouse this morning. I think I made a good impression.”

Castiel Novak 

Cas was certain he knew what was going on the moment Dean mentioned he talked to Jimmy. He knew his brothers enough to know they were meddlesome little shits, so when he arrived for his shift at the bakery, he was intentionally going to act clueless when Dean would “randomly show up for pie.” Now he wasn’t sure how they found out about the pie thing, but Cas wouldn’t put it past his brothers to do some stalking. And he was going to tell Dean about the plan, but not just yet. I mean how else would he prank his best friend. 

“Good, you’re here,” Gabriel said as he walked into the bakery. Pies lined every portion of the display, which was not unusual, but the new, experimental pies were out too. 

“Are you stocking up for the apocalypse or?” Castiel headed behind the counter prepared for Dean to walk in at any moment.

Gabriel shrugged in response. “You can never have too much pie.” 

The bell to the shop rang revealing the one and only Dean Winchester at the doorway, admiring the beautiful pies. 

“Hello, Dean.” Cas sent him a short wave. 

“Hey Cas. Where’s Jimmy?” he looked around in confusion. 

“He’s out sick at home. Apparently he caught something after his first class.” That part was true enough, Jimmy told him to tell Dean he was out sick. Honestly, the planning on the scenarios his brothers were not too bad. In fact, he was kind of proud of the brilliant planning from his brothers. 

“So, Cas how was your day anyway? You looked like you were contemplating homicide,” he hesitates before adding a quick, “in a good way, of course.”

The conversation continued for a while. Meanwhile, Gabriel was out “checking supply” when in actuality was probably spying on the pair using the security cameras. The bell to the shop rang again, revealing...a moose. Not actually, of course, but the man sure could pass for one, having to duck under the door frame. 

“Hey, Dean.” Giant said, sliding into a seat besides Dean. 

“Heya, Sammy,” Dean said before turning towards Castiel. “You haven’t met Sammy yet, have you?” Cas gives him a quick shake of the head. “Cas, this is my baby brother, Sammy. Sammy, this is my friend Cas.”

Sammy turned to face Cas, holding out a hand. “Sam,” he introduced. “Pleasure to meet you.”

Castiel accepted with a quick, “Castiel,” of introduction. 

“So, you and Dean seem to be close, huh?” Sam looked back at Dean and then back to Cas. 

Castiel gave a sharp nod. “I guess one could say that.” 

Sam’s eyes glittered with mischief. “Say we have a drink or two at the campus bar tomorrow.”

**Notes for the Chapter:**

> Thank you for reading! Next chapter is gonna be a fun one ;) And I’m including the POVs in order for it to work better as there are going to be a lot of POV shifts


	6. Under No Circumstances Should You Take Planning Advice From Sam, Jimmy, Or Gabriel

**Summary for the Chapter:**

> The plan goes south, obviously, and Dean and Castiel prank their brothers in retaliation. Much shenanigans, much fun.

“Dammit, Sammy. Of course he decided to set us up.” 

“So you got the plan?” Cas asked him, placing a hand on Dean’s shoulder. 

Dean’s eyes lit up with excitement, so similar to Sam’s. “It’s go time.”

Sam Winchester 

The campus bar was relatively okay, most students preferring to buy booze from their separate sources and consume copious amounts of alcohol at frat parties and such. (The author knows nothing about college stuff, so take this representation as college fanon). Dean and Castiel were yet to arrive and the plan was going quite smoothly if you asked him. Alas plans never really went well. 

The first few hours were okay, Dean and Cas guzzling down beer by shot by beer. The drinking has footed so far of the rails that Sam could feel the hangover from a mile away and let him tell you, it wasn’t pretty. About 2 hours into the evening, Sam had mysteriously, “went to the bathroom” and hadn’t been out for another 2 hours. The truth of the matter was that one Sam Winchester along with Gabriel and Jimmy Novak were squished together in an empty closet at the bar, staring at Sam’s computer wedged between their laps. 

The tape was great at first, the boys watching as the pair laughed and flirted a little. Then things began to get heated. 

Castiel raises his fist, punching Dean square in the jaw. 

Sam winced at the sight, imagining the bruise Dean would probably be sprouting by the next day. He turned around to see Gabe and Jimmy staring at the screen in shock. Apparently this type of behavior was quite unexpected of Cas as the two brothers eyes were as big as dinner plates. 

“What the f-”

Dean Winchester 

Back at the bar, Dean held back silent laughter at the staged punch. God, Sam was probably gonna kill him when he found out. 

Gabriel Novak 

The video continued playing to show the events of the evening. The slap was pretty out there, Gabriel thought. Who knew Castiel was an angry drunk? But what was most perplexing was what had happened after the slap. Dean pulled Cas into a haste kiss before pulling apart again. Some cheesy lovey dovey look passed through both of their faces before they start full on making out in front of the screen. 

Jimmy Novak 

There was one thing going through Jimmy’s head at that moment. Well, two really. Number one was that, “that’s my brother!” and the corresponding celebrations for his twin finally breaking out of his shell. The other was that this video was an emotional roller coaster. 

And that’s when it hit him. 

Jimmy looked to Gabe and Sam to be met by equally confused faces. “Guys,” he said, bringing their focus onto him. “I think we’ve been played.”

Castiel Novak 

If there was one thing Castiel was most proud of during the entirety of his college career, it was the face made by Gabriel, Sam, and Jimmy. The looks of shock, confusion, and betrayal was a combination worth seeing. Their jawas had nearly dropped to the floor as Jimmy pointed his index finger angrily. “You, played us.”

Castiel crossed his arms, staring at his twin. “That is correct. And?”

Gabriel let out a short bark of laughter. “I knew I’d get some bad influence on you!” He tilted his head back to let out more hysterical laughter before Sam interrupted. 

“So, you guys knew what we were planning all along?” 

Dean shook his head, sipping at his beer. “No. Cas figured it out,” he turned to face Castiel, giving him a questioned stare. “When did you figure it out?” 

Cas answered, stating. “I knew since you told me Jimmy had talked to you. Knowing my brothers, I had expected worse.”

“Wait,” Dean looked into Cas’ eyes. “You knew for that long and didn’t tell me.” He sent him an overdramatic hurt look. In return he receives a slight punch to the shoulder from Castiel before a smile creeps onto his face and Dean pulls Cas into him, The group dropped into silence at the display, minds thoroughly blown at the lack of obliviousness that shout have been present. 

Gabriel was the first to break the quiet. “Wait, did you two bozos start dating without the obliviousness?” He turned to face Sam and Jimmy. “Now, I don’t know about you, Sammy, but in my experience, my brother never directly tells anyone about his emotions.” 

Sam nods towards Gabe. “Yeah that sounds like Dean.”

“Bitch.”

“Jerk,” Sam replied. “But in all honesty, how did you guys get over your emotional repression?”

“Well,” Cas began, “in the beginning, we did bounce around each other like idiots until Meg trapped us in a supply closet by accident.” 

Jimmy hissed at the mention of Meg, claiming, “Demon cat.”

Castiel rolled his eyes. “And the fact that the supposed ‘demon cat’ was able to get us to admit our feeling better than you guys says something.”

“...Touche.”

And so, there went Operation Destiel. A sort of failure, sort of success, but a total waste of everyone’s time. No, seriously, why are you reading this shitty filler fic? Go back to your 100K fanfic laying unread in one of the billion tabs open on your device. Jimmy, Cas, Gabe, Sam, Dean, Jo, and Ellen’s coffee all wish you happy reading and a thanks for stopping by this fluffy crack fic on your way to Angst City. Bye!

**Notes for the Chapter:**

> Thank you so much for reading wonderful humans! (at least I assume you to be human)

**Author's Note:**

> Thank you guys so much for reading! This is the second pic I've completed and am pretty proud of. Again, check out TheBadassIsIn's pic, The Whole Damn RoadHouse Knows:)


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